Trifluoroacetic acid → HCID 22280107, compound

HRID 1063709Notes

Reaction equation

HRID 1063709 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:16][CH:15]=2)=[CH:8][C:7]=1[CH3:28].[K+].[Br-].C(O)(C(F)(F)F)=O>C(#N)C.O>[CH3:28][C:7]1[CH:8]=[C:9]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:16][CH:15]=2)[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]([OH:29])=[O:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 253877Potassium BromideHCID 20827006HCID 20827006, compound

Product 1

HCID 22280107HCID 22280107, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared in the manner analogous to Example 1 using 60A. mp 150° C.; IR (KBr) cm−1: 2917, 1723, 1605, 1511, 1490, 1217; 400 MHz 1HNMR (DMSO-d6): δ 12.95 (brs, 1H), 8.49-8.55 (s, 1H), 7.73-7.81 (m, 1H), 7.40-7.48 (m, 1H), 7.24-7.33 (m, 1H), 7.00-7.19 (m, 4H), 6.83-6.93 (m, 2H), 6.69 (d, 1H, J=8.5 Hz), 5.08 (s, 2H), 4.62 (s, 2H), 4.00 (s, 2H), 2.08 (s, 3H); HPLC: area %=96.24, r.t.=1.95 min., γ=214 nm, mobile phase=acetonitrile/water with 0.10% TFA; MS m/z 396 (M+1). Anal. Calc'd for C22H21NO4S: C, 66.82; H, 5.35; N, 3.54. found: C, 66.12; H, 5.09; N, 3.44.

Sources & evidence

ORD record
ord-65f1c11bbd354605ba25b99bc9c5f5ab
Source dataset
uspto-grants-2005_11
Patent number
US06964983B2

Reaction notes

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